Fluorine compound



ethyl-ethyl ether and ?atented Dec. 14, 1943 2,336,921 FLUORDIE COMPOUND Anthony F. Benning, Woodstown,

Wilmington, Del... Kinetic Chemicals, Inc., Wilmington, corporation or Delaware seph D. Park,

No Drawing.

N. 3., and .lo-

assignors to Del., a

Application December 13, 1941,

Serial No.1422,871 6 Claims. (Cl. 260-614) A. This invention relates to 2,2,2-tri-fluorov to fluoro-alkyl-alkyl ethers containing the group CFs, and to a method of preparing them.

B. It has heretofore been proposed by Swarts, Centr. (1901) II 804 and (1911) II 848 to make ethers from fluoro brom ethanes. The reaction of the chlor compoundsdoes not proceed according to the conditions prescribed by Swarts.

C. It is an object of the invention to prepare the fiuoro ethers from fiuoro-chlor aliphatic hydrocarbons. Another object of the invention is to prepare ethers having the group CFs, and particularly 2,2,Z-tri-fiuoro-ethyhethyl ether.

D. The objects of the invention are accomplished, generally speaking, by reacting a fluorochloro-alkane with an alkali metal alkoxide at a temperature oetween about 100 C. and about 175 C. under pressure.

E. In carrying out the preferred form of the reaction one of the reagents is a tri-fluoro-alkyl chloride having the group CFs and one or more groups CH2. The number of CH2 groups may range up to eleven, but above five there is some tendency for side reactions to occur. Among the compounds of this type are tri-fiuoro-ethyl chloride, tri-fiuoro-propyl chloride and tri-fi uorobutyl chloride. The other reactant is an alkali metal alkoxide, in which the alkyl group may have from one to twelve carbon atoms but has preferably from one to six.- The alkali metal is preferably sodium but may be any of the others, although the substitution of others should be attended' by modifications in the reaction conditions designed to produce optimum results. Among the more useful of these groups are sodium propoxide and sodium butoxide. Sodium thioalkoxides may also be used where thio ethers containing fluorine are desired.

F. The following example is illustrative of the reaction:

Example or-awn 1.002115, in which n is a About 10 parts by weight of Cal-IsONa in was obtained. This material had a boiling point of 78.7 to 79.5 C. The molecular weightof this material determined cryoscopically was found to be as compared to a calculated value of 128. G. In general it is desirable to carry out the reaction in liquid phase and in the absence of water. Consequently, non-aqueous solvents, such as absolute alcohol and anhydrous saturated hydrocarbons may be used as reaction media.

H. Economically this invention is better than the method of producing ethers of this type by the use of fluoro-brom derivatives. Another advantage is the production of new and useful compounds such as CF3CH2OC2H5, CFsCI-IzCHzOCzI-Is, and CFaCHzOCsH-r. These new compounds have a variety of commercial uses. Some of them are excellent refrigerants and solvents.

I. As many apparently widely different embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that we do not limit ourselves tothe specific embodiments thereof except as defined in the appended claims.

We claim:

1. The compound represented by the formula CFaCHzOCaI-Is.

2. The compounds represented by the formula digit from 1 3. The process of preparing 2,2,2-trifiuoroethyl-ethyl ether which comprises reacting 2,2,2- trifiuoro-l-chlor-ethane with an alkali metal ethoxlde at elevated temperature under pressure.

4. The process which comprises reacting 10 parts by weight of C2H50Na in alcohol solution with about 40 parts of CF3CH2C1 at about 130 C. under drowning the products of the reaction in cold water, washing and drying them.

5. A trifluoroalkyl-alkyl-ether having a boiling point of 78.7" to 79.5 C. and a molecular weight, determined cryoscopically. of 130.

6. The process of preparing trifiuoro-alkylalkyl ethers which comprises reacting an alkali metal alkoxide with CF3(CH2)11.C1, in which n is an integer from the group consisting of 1 to 5, under pressure and at a temperature between about 100 C. and C. l

ANTl-lONY F. IBENNING. JOSEPH n. PARK. 

